


The Things We Do For Love

by tinyspaceurl



Category: Supernatural
Genre: Anal Sex, Angst, Blowjobs, Bottom Dean, Caretaker Sam, Comforting Sam, Crossdressing, Depression, Fingering, First Time, Fluff, Hurt Dean, John Winchester's A+ Parenting, Lingerie, M/M, Panties, Prostitute Dean, Prostitution, Rape/Non-con - Freeform, Smut, Suicidal Thoughts, Suicide, Wincest/Weecest - Freeform, depressed thoughts, handjobs, money issues, sam bottoms his first time
Language: English
Status: Completed
Published: 2016-01-26
Updated: 2016-04-10
Packaged: 2018-05-16 15:22:44
Rating: Mature
Warnings: Major Character Death, Rape/Non-Con, Underage
Chapters: 13
Words: 9,139
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5830672
Author URL: https://archiveofourown.org/users/tinyspaceurl/pseuds/tinyspaceurl
Summary: <blockquote class="userstuff">
              <p>This is the story of a boy who loses his innocence at the age of 13, a boy who loves his brother too much to see him suffer. This is the story of a boy who would do anything to keep the light of his life healthy and happy, even if it's doing something as dirty as prostitution.</p>
            </blockquote>





	1. Chapter 1

It was happening again. The money was low, only five bucks left, when Dean counted this morning. The shelves were bare, and Sam was starting to ask for dinner. Dean couldn't find it in himself to tell his baby brother that there wasn't going to be any dinner tonight. 

There was an idea that had been niggling his brain for a few days now, but the very thought scared him. Dean didn't think he could ever bring himself to go out on the street in skimpy clothes and sell himself. 

But the longer Dean thought about it, and the longer he watched Sam discreetly rummage in the empty pantry for food, he found himself thinking that maybe it wasn't such a bad idea. 

He could just go out, do his thing, and bring home takeout. Sam wouldn't go to bed hungry, and Dean wasn't exactly losing something important to him. 

He sighed and stood up, giving Sam a small smile as he walked into their room. He rifled through his clothes until he found a skirt he'd swiped from a thrift store a few towns back, and a tight black t-shirt. He clutched the items close to his chest and walked back out to the living room. "Alright, Sammy. I have to head out, but I promise I'll be back soon. Stay inside, don't answer the door, and just... try to hold out 'til I'm home, alright?" Dean said, hand on the doorknob.

Sam nodded at Dean and gave him a reassuring smile. "Okay, Dean. See you soon," he said before slipping into a chair and pulling out a book from the pocket of the hoodie he was wearing. 

Dean sighed and gazed at his brother for a long moment before walking out of the house. He looked around quickly before stripping, setting his clothes on the porch, and changing into the pleated white mini-skirt and black shirt. 

Dean sighed shakily and began walking hesitantly towards the busier streets. He passed quite a few other boys and girls a little older than him desperately throwing themselves at anybody who walked by. 

Dean stood close to a bar, watching the men inside carefully as he tugged on the end of his skirt. 

After a few minutes, he'd picked out a suited man to try and get. He looked rich, and drunk enough to fuck a minor. Boy was Dean right. 

The man stumbled out soon after Dean spotted him, and the teen darted forward, grabbing the guy's sleeve and looking up at him bashfully. 

"'Scuse me, sir. I need some help," Dean said in a sweet voice. The man turned and eyed Dean slowly before smirking. "I think I can ah... help you out, sugar," he drawled.

Dean smiled innocently and tilted his head. "I'd really appreciate it, sir." he said. The smile faded quickly as the man roughly grabbed Dean's arms and pinning him up against the brick wall of the building.

"Ah, easy man! I'm-" Dean was cut off by his own yelp of surprise at his skirt being pushed up and his bare ass exposed to the chilly air. 

The man spit into his hand and Dean flinched at the sound of the guy stroking himself. 

He was beginning to regret doing this, and it only increased when two fingers were suddenly shoving their way into his hole. 

"Oh fuck-" he hissed in pain and scratched at the wall as the man made quick work of scissoring him open. 

Just as quickly as the fingers were pushed in, they were gone, and replaced by the blunt head of the man's cock shoving into his tight heat. 

Dean was whimpering and clawing desperately at the wall by the time the man started thrusting, and he thought the pain would never leave. 

He let his mind go blank as he was fucked into from behind, the man's fingers bruising his tender, unmarked flesh, his fingers scraped raw and bleeding, and his own cock bobbing half-hard between his firm, milky thighs. 

There was no pleasure in this fuck, and he was hoping it was over soon. He still had a brother to get home to. 

Finally, the man's breath hitched, and he slammed into the whimpering boy beneath him before pulling out and shooting his load all over Dean's thighs and boots. 

When he was spent, he tucked himself back into his boxers, pulled out a two twenties, and folded them into one of Dean's hands before stumbling to his car.

Dean slowly straightened up, crying out once in pain but quickly silencing himself and limping home, past the other desperate teens, past the shady alleys, all the way home.

He leaned against the wall and changed quickly after wiping himself down with the skirt, and then made his way inside. 

Sam was asleep on the couch, so Dean tossed the dirty clothes into the laundry room, hobbled over to his brother, and carried him to bed. 

The money Dean set on the counter, and then he dragged himself into the bathroom, where he stripped, scrubbed himself raw in the shower, and cried. 

"All of this was and will always be for Sammy."

He'd be lying if he said things went uphill from there.


	2. Chapter 2

The morning after Dean's terrible night, Dean could barely get out of bed, let alone drag his sorry ass to the grocery store for food. 

He had to, though. Watching Sammy sleep peacefully next to him, ribs beginning to show even under the shirt he'd stolen from Dean. 

So Dean pushed himself up, swung his legs over the edge of the bed, and forced himself to stand. His knees buckled from the pain in his ass, and he fell with a soft grunt. 

"Dammit... I've taken out a werewolf before- I can get through this," Dean muttered as he stood back up. And then, slowly but surely, he walked out of the bedroom and into the kitchen. 

Shaky fingers gripped the 45 dollars he had, and shaky legs allowed him to sit gingerly on the floor to tie his boots. 

Dean didn't bother changing out of his sweatpants and hoodie, mostly because it'd take too long with the pain below his waist, and he wanted to be back before Sam was awake. Which pretty much meant he had an hour to walk to the grocery store down the street, get groceries, and walk back home with the grocery bags. He hoped he could do it. 

Dean pushed himself to his feet, swaying slightly as he opened the front door. Sadly, he forgot to take into account that Sam was normally a light sleeper. This morning was no acception. 

The minute the front door creaked open, Dean heard his brother's voice calling for him, getting louder as the boy padded out to the living room. 

Dean had no choice but to stay where he was while his brother took in the sight before him. 

"Where ya goin'?" Sam asked, smoothing down his hair that was getting too long in Dean's opinion and grabbing his own scuffed up sneakers. 

Dean sighed softly. "Store. Got some money last night," Dean responded, showing Sam the bills in his hand and reaching for Sam with his free hand. 

"Grab your jacket if you're coming with. 'S chilly," Dean ordered, knowing full well that Sam was going with him. 

Som complied, shrugging on a hand-me-down leather jacket from Dean. The sleeves covered his hands, and Dean found the sight incredibly endearing. 

Dean gripped one of Sam's covered hands in his own and nudged open the screen door with his hip. He took a deep breath as a cold breeze blasted him in the face, and limped outside on shaking legs. 

He could feel Sam's eyes on him, and just hoped the boy wouldn't ask questions. 

"I tried to stay awake, but my tummy hurt and I was tired, so I just fell asleep," Sam said after a few minutes of silence. 

"Sorry, kiddo. I was out later than I thought."

"It's okay, De. As long as you come home." 

Alive. 

The word was left hanging between the brothers in the silence of the morning, and Dean sighed shakily. "I'll always come home, Sammy. Even if I'm bruised, cut-up, angry, sad, happy, I'll come home. Even if I know the sight of me will scare you shitless, I'll come home. To you. Always," Dean promised his brother. And he meant it. Every damn word.

Sam nodded and pulled his hand away from Dean to hold the older boy's hand up. "Your fingers are torn up. You left blood on the sink last night, I saw it when I got up to use the bathroom. How exactly did you get that forty dollars?" Sam asked softly.

Dean was silent as he kept limping along. What the hell was he supposed to say? 'Yeah I let some drunk guy take my virginity to get you some food'? Sam couldn't find out that he-

Dean's thoughts were interrupted by the rumble of a car pulling up beside them. Dean stepped protectively in front of Sam as one of the windows was rolled down.

In the car was the guy from last night, a concerned frown on his face. "You boys need a ride somewhere?" he asked. 

Dean swallowed hard as the guy gave him a look that showed that he fully recognized Dean. "Uh, yeah. We do. Thanks," Dean mumbled, catching sight of a young girl in the back seat. 

"Hop in then, kids," the man said kindly. Dean gave him a nod and opened the back door for Sam before awkwardly sitting in the passenger seat. 

"We're goin' to the grocery store up the road a ways," he said after a moment. The man just nodded and headed in that direction. 

Dean could hear Sam and what he presumed to be the man's daughter talking in the back together, but he didn't attempt to listen in. The throbbing all through his lower half was way too distracting. 

They arrived at the store quickly, and Dean shot the man a quick thanks before clambering out of the vehicle and guiding Sam into the store without a glance back. 

***

Hours passed, and after eating breakfast and lunch, Dean was laying on his stomach on the couch with Sam on his legs and a horror movie playing. 

Throughout the day, the temperature outside just kept dropping, so the boys had the heat cranked up on high.

Sam turned off the TV suddenly and turned to Dean. "De, tell me what you did last night. Please. I can take it," he said pleadingly.

Dean closed his eyes and sighed heavily. "Sammy I... I just can't. Please, drop it. When you're older... you'll understand. Maybe.


	3. Chapter 3

Dean sighed as he watched Sam studying for some history test at school. His hair was curled around his ears and across his neck from the sweat and humidity in the air both inside and outside the shitty motel room John had dropped them off in. 

Dean checked the time as he stood up and bit his lip. "Sammy, how much money we got left?" he asked as he walked over to his brother. Sam shrugged and glanced at Dean. "Ten bucks I think. It's enough for dinner, and Dad said he'd be back in two days. You don't have to go...do whatever you do to get us money," Sam muttered.

Dean already had his bag of supplies in his hand, and he set it down for a minute to run a hand through Sam's sweaty hair and press a light kiss to the back of his neck. 

"I'll be back in an hour. Keep an eye on the clock, and if I'm not back, call my buddy Jake. Number's on the fridge. Do NOT call Dad. Alright?" Dean said as he opened the door.

"Okay but-"

Dean was out the door before could hear the rest of the objection.

***

"C'mon, get on your knees, bitch."

Dean complied, dropping to his knees and staring up at the man before him through his lashes. 

"Take it out and suck it, babe."

Dean sighed and slid his gaze to the clothed dick before him. He undid the man's belt and pulled his jeans and boxers down slowly. 

Grimacing, he took the man's dick into his mouth slowly, inch by inch, until it hit the back of Dean's throat and he gagged slightly. 

Dean bobbed his head slowly, keeping his tongue flat to rub the sensitive underside of the man's dick. 

Suddenly, the man's grimy fingers were curled into Dean's sun-bleached hair, and forcing his head to bob at the pace the man wanted. 

Telltale grunts and the disappearance of the man's dick in his mouth told Dean the man was about to come. He closed his eyes, parted his lips slightly, and barely flinched as hot fluid splattered over his face, in his hair, and dripped into his mouth. 

"Fuck you look even hotter with come on your slutty face. Here," the man said gruffly, and Dean heard the crinkle of bills being thrown at him and then receding footsteps. 

Dean opened his eyes, grabbed up the money, and slid his bag close. He pulled out a cloth and wiped the come off his face and out of his hair before standing up and practically skipping to the nearest store and fast food restaurant.

***  
When Dean walked back into the motel room later, he only had time to set all the bags on the table before he was enveloped in the warm weight and smell that was Sammy. 

"Oh Dean I was getting worried it was five minutes to seven and you were still gone and I was gonna call Jake but you came back and you seem okay..."

Dean let Sam babble on as the boy climbed on him, wrapped his tiny legs around Dean's waist, and inspected his face. 

Suddenly, the grin faded from Sam's face and he stared at Dean's hair. "What's that?" he asked. 

Dean frowned, a bolt of panic going through him as he tried to figure what Sam was looking at. "Uh... what's what, Sammy?" he mumbled.

Sam pushed his fingers into Dean's hair, and when he showed them to Dean, they were coated in white fluid. "What the hell is this?" Sam snapped.

Dean froze as Sam angrily wiped his fingers on his jeans. Guess he didn't get all the come out of his hair earlier. "Dean, you gotta tell me how you're getting the money. Now." Sam whispered.

Dean nodded slowly in defeat and led Sam to sit on the couch. Dean sat beside him and stared at his hands. "It started last year, when you were starving and we had five bucks to our names..."


	4. Chapter 4

Dean couldn't even look at Sam the day after he'd told the kid about the way he got them money. Sammy had been silent all day, but Dean could feel those hazel eyes burning into him, and he knew Sam needed to say something. 

"Spit it out, Sammy. I know you wanna say somethin'," Dean muttured. He could feel the couch dip when Sam sank down next to him, could feel his little brother's stick-like arms wrapping around him. Dean just leaned on Sam, waiting for the boy to say what he needed to. 

"I just... don't understand... why you would resort to... that, for me. I'm a kid. I can survive without food for a few days, or mooch off someone at school or the store. Selling yourself isn't the answer. You could get hurt... or get a disease... or get killed! Promise me you won't do it anymore, Dean. Promise me you'll find another way to get money."

Dean closed his eyes and leaned back on the couch, running his fingers through Sam's curls. "I can't make a promise that I know I'll break. And trust me, I won't get sick. They don't touch me 'til I know they have protection," Dean said softly, hearing Sam's sigh beneath his chin.

***  
John came home that night, but Dean wasn't worried about him finding out. He'd made Sam swear that he wouldn't tell John, so he felt he was safe. 

Thankfully, John went straight to bed when he got home, after muttering about leaving early tomorrow, so Dean was currently monitoring Sam while the boy brushed his teeth in the bathroom. 

"Hurry up, Sammy. I'd like to get a few hours of sleep tonight, y'know," he teased, winking at his brother in the mirror. Sam rolled his eyes, but finished brushing his teeth quickly. 

While the younger Winchester got ready for bed, Dean washed his hands and face before scrubbing at his teeth and shucking his jeans off. 

When he finished, he put his toothbrush in his bag and pulled on a Metallica shirt and pajama bottoms. Dean crawled into bed beside Sam and pulled the boy to his chest, nuzzling his soft hair gently as he eased into sleep. 

Tomorrow would be a very long day.


	5. Chapter 5

**Summary for the Chapter:**

> Set 3 years after Dean tells Sam. Dean's 17, Sam's 13. Big things happen.

Another town. This one 5 states away from the last. It was all the same to Dean, though. Just people for him to get money from. Just opportunities to help Sam. 

John rented a house this time, said they would be here for at least 2 months. He'd be juggling a job and reasearching the hunt, so he said he'd stay at a motel. Sam would be at school, and it was Dean's job (like always) to watch out for him. 

At least Dean had time to himself. Bathing, fingering himself, buying skirts and panties, and maybe, just maybe, finding a sex shop and grabbing more supplies. After 4 years of this, Dean knew what to expect. He knew that no matter how Dean rationed the money, it was gone as quickly as it came.

***  
The money lasted two weeks. Two damn weeks, and Dean was sneaking out when Sam was asleep, knowing the boy would stop him. 

Dean was wearing a tight shirt, as usual, and a black mini-skirt with lacy white panties. He'd be lying if he said he didn't like the feeling of the panties, the swish of the skirt over his hairless thighs, the glitter and eyeliner on his face. 

Tonight was different than usual, though. Men paid no attention to Dean, no matter what he did. So he walked down the street, more lost in his thoughts than he was looking for a fuck. The sound of heavy footsteps caught his attention, but he didn't turn. Better to keep them curious. 

Large hands grabbed his arms suddenly, smashing him against the nearest wall. "Hey! Watch it, man, I'll kick your ass if you hurt me," Dean warned. 

The guy chuckled, and Dean froze as he recognized the voice. This was his dad's current boss. No way in hell could this guy fuck him, not if he was close to John. 

Dean began struggling, desperate to get away, but the guy saw it as a game. "Aw, sweetheart, you into the struggling thing? Well me too," he drawled as he pushed Dean's shirt up and tore the panties as he pushed them down. 

Dean was panicking, debating on screaming as the tell-tale crinkle of a condom was heard, but he had no voice. He pushed off the wall and stumbled away from the guy, only to be slammed into the wall, head knocking hard enough against it to make Dean pass out. 

***  
When Dean came to, the guy was gone, and there were bills tucked into his shirt. He whined as he felt stickiness on the side of his head, and cried out when he tried to stand. Looking down, he saw dried blood on his thighs and bruises littering his body. He trembled hard and hugged his knees to his chest, pulling out his phone and calling Sam. 

"Hello? Dean where are you? Is everything al-" 

"Sammy... Need you to come get me. Things didn't go well last night... I'm so sorry..."

"Dean what the hell happened?!" 

"Sammy- Sam I was raped. I can't stand up, I need you to help me home." 

"A-Alright big brother. I'm on my way." 

Dean nodded and hung up, setting the phone beside him and letting out broken sobs. 

How could this happen?


	6. Chapter 6

When Dean saw Sam, sweet, awkward Sam, running towards him with two bags, Dean felt guilty. Guilty for putting his 13 year old brother through this, all because Dean was too weak to fight the guy off. His shirt was stained with blood, his skirt a darker black, and his panties a torn, bloody mess around his thighs. 

Sam crouched beside Dean and cupped his face, looking him over carefully before opening one of the bags and pulling out rubbing alcohol, a cloth, and bandages. "Y-you were raped?" he asked as he dabbed the cut on Dean's temple clean. Dean winced in pain and nodded. "Mhm... It was Dad's boss... I couldn't risk him bragging or something and Dad overhearing it... But I couldn't defend myself. Now it's too late, and all my fault," he rasped. 

Sam stopped for a moment to cup Dean's face, tears in his eyes. "Do /not/ blame yourself for this disgusting man raping you, Dean Winchester. You /never/ say that this bullshit is your fault ever again, okay?!" Sam said, eyes gold-green fire. Dean nodded, tears rolling down his cheeks as he clutched his little brother tightly. 

Dean was silent aside from whimpers and sniffles as Sam cleaned him up. The boy hesitated once he cleaned Dean's thighs of blood, and looked up at Dean. "I'm not cleaning anything else in the open. I'll help you home..." Sam said. 

Dean nodded and braced himself on the wall as he stood, pain shooting through him and something warm rushing down his thighs. "Dean- De you're still bleeding I- I- gotta call someone to help us..." Sam said, holding Dean's weight and dialing a number. 

"Not Dad, right?" Dean said desperately. Sam nodded and rubbed Dean's side. "Not Dad. My friend Erin, his parents can help you. They deal with... with rape incidents," Sam promised before talking into the phone. 

Dean waited, staring blankly at the money in his fist as Sam spoke in hushed tones. Minutes later, Sam smiled at Dean. "Hey, they'll be here in a few minutes, De. You good?" Sam asked softly. 

Dean nodded and nuzzled Sam's hair. "I'm fine, baby," he said, the nickname just a habit. Sam flushed and grinned nonetheless, holding Dean tighter as they waited. Dean passed out just as the car came into sight. 

***  
After a while, Dean found himself curled up in a blanket on what seemed like an exam table, cold gloved fingers probing the inside of his ass. He whined and tried to squirm away, movements sluggish and whole body numb. 

"Relax, sweetheart. I'm just putting ointment on to help you heal in there. You're perfectly safe," a soothing voice said from behind Dean. 

"S'mmy... 'ere's S'mmy?" Dean slurred, blinking at the soft pink of the walls. 

"Sam's right outside, honey. You can see him in a minute," the woman promised.

Dean nodded, jerking forward as the fingers disappeared, leaving him embarassed as he ached for something inside him. 

"Don't let anything in there except for your fingers to apply more ointment for the next few weeks, alright, Dean?" The woman said, appearing in front of Dean with a soft smile. 

Dean nodded and let the woman help him to his feet and into sweats. "We'll drive you home. By the way, Dean, none of this is your fault. That man should have realized you didn't want sex and backed off. I'm sorry he forced you into it. Don't blame yourself..." 

Dean just nodded and smiled weakly. He knew that no matter what anybody said, he'd blame himself for this incident for a long, long time.


	7. Chapter 7

**Summary for the Chapter:**

> Set in John's point of view.

Another day. That was John's first thought as he drove to work. Just another ordinary day. Well, ordinary for him. He knew that between work and research, he'd have to check on his boys, make sure they were doing good on money and food. He'd get on Dean about getting a job, make some extra money just in case. 

John pulled into the garage he was working at and climbed out, patting the top of the Impala before he walked inside. He nodded to his co-workers and his boss, who was grinning from ear to ear as he talked to one of his buddies. 

John just shook his head and chuckled, running his fingers through his hair before getting to work. 

***  
When lunch break came around, John sat outside with the others, listening to their conversations as he scribbled in his notebook. A few minutes after sitting there, the familiar sound of a truck pulling up drew John's eyes up to it. He saw his eldest son behind the wheel, grinning as he waved to John. Sam was the one who hopped out of the front and scampered over to John with a paper sack full of his lunch. 

"Hi Dad. Dean's not feelin' good, so I'm giving you your lunch today," Sam said, smiling at John as his eyes scanned the other men. 

"Well, thanks kiddo. Tell Dean I'll be down after work to check up on you boys, alright?" he said, ruffling Sam's hair. 

Sam huffed and smoothed it down before nodding and jogging back to the truck. "Bye!" John called before the truck pulled away. 

John chuckled softly and took the sandwich out of the sack, eating it slowly as his boss launched into a story about his night. 

"So I saw this kid, no more n' 17 jus' walkin' down the street in a skirt and combat boots, right? And I thought it was a girl with one of those short haircuts, but then he turned, and I could tell that it weren't no girl in that getup. Just a twink lookin' for fun, by the way he was smirkin'. So I grabbed 'im, pinned him to the wall, and he started pretendin' like he didn't want it. I could tell he did though. Went a little too rough, but he wasn't no worse for wear. Jus' some blood and bruises." 

John frowned and stared at his boss in slight disgust. He had nothing against gays, honest, but the fact that the kid was 17 and prostituting himself, and that his boss still had sex with him bothered John a lot. Not some of his other co-workers though. A taller man, Matt, leaned forward and tilted his head. "What'd he look like?" 

"Ah, green eyes, lots of freckles under the glitter he had on, and real short blondish hair. Spiky, kinda like a faux hawk. Jus' real cute," John's boss drawled. 

John tensed, because that really sounded like his son. He tried for a question and cleared his throat. "Did he have any jewelry on?" he asked, getting astonished looks from the other men. 

"Uh, yeah. He did. Had a silver ring on his right ring finger, and I think a necklace with this real weird gold amulet on it. Why?" 

John swallowed, a feeling of dread in the pit of his stomach. "Jus' wondering. Hey, I gotta go check on my boys. I don't know if I'll be back," he said before running to his car, lunch abandoned on the table. 

He drove to the house he was renting out and climbed out, running inside and looking around wildly until he spotted Dean on his stomach on the couch. 

"Dean!" John yelled, shaking the boy roughly before unzipping Dean's duffel and rummaging through it. "Wha'? Dad? Dad what the hell!" Dean said, clumsily reaching for the skirt and tube of eyeliner John was holding up. 

"Dean don't tell me you've been /prostituting/ yourself..." 

Dean was silent, and John felt the dread in the pit of his stomach evolve into horror. 

"Dean why- Does Sam know?" John whispered. Dean, his poor boy Dean, had silent tears rolling down his cheeks as he nodded. 

"Dad I'm sorry... It was the only way I could get money fast... you never leave enough... I'm sorry," Dean whispered as John pulled his eldest into a hug. 

"You shoulda told me I wasn't leaving enough instead of... of selling yourself on the streets! And you were raped, because I didn't leave enough- Dammit Dean this is my fault!" John said. 

Dean shook his head and sniffled. "No 's not, Dad..." 

"It /is/, Dean. But not anymore. I promise I'll leave as much money as I can. From now on, you won't have to do this. I love you, Dean. And I'm so, so sorry."


	8. Chapter 8

**Summary for the Chapter:**

> Dean's 18th birthday. He gets some special gifts from Sam and John.

Normally Dean's birthday wasn't a big deal. Just a pat on the back from John, maybe a gun or blade, and a little gift from Sammy. It's what Dean came to expect. Easy and simple, nothing too big, nothing too special. 

Of course though, John and Sam had to go and make Dean entering legal adulthood such a big deal, leaving Dean all flustered and embarrassed. 

Dean woke up the morning of his birthday to the sound of a truck pulling into the gravel driveway of the house John was renting out. Confused, Dean shook Sam awake beside him and stood up, feet freezing on the icy wood floor. 

He walked out of the bedroom, squinting against the light flooding in through the huge windows covering one whole wall of the house. 

Dean thought this was the nicest house they'd rented out so far. Two bedrooms, two working bathrooms, a functioning furnace, and an open kitchen and living room. The couple that owned the place were old friends of John's, which helped a lot, but Dean did some 'work' with the husband to make the cheap rent official. 

He shook away the thoughts of his night two days ago and stood in the front door, squinting at John climbing out of a rusty pickup. "Dad why do you have that?" Dean called after pulling open the front door. John turned and grinned at his eldest, walking over and stomping the snow off his boots before walking inside. "Let's eat breakfast first. Then I'll tell ya," he said. 

Dean shrugged and followed his dad into the kitchen, smiling at Sam sitting on the counter. He got a dimpled smile in return and chuckled at Sam's complete innocence. 

John was talking as he rummaged through the fridge, and Dean turned his attention to the older man. "We all know I can't cook to save my life, but Sammy here decided he was gonna stay up late and make us- you in particular, Dean, breakfast. Just gotta heat it up. Bacon, pancakes, sausage," John said as he pulled covered plates out of the fridge. 

Dean stared at John's hands distractedly, studying the healing cuts over his knuckles. Last month, one of John's former bosses had raped Dean. Before they left town, Dean and Sam had watched their father beat the shit out of the man without hesitation or regret. It kind of scared them, but they wouldn't say it.

Dean grinned as he sat at the table, John sitting across from him and Sam beside him as they ate. "S' good, Sammy," Dean mumbled around a mouthful of food. Sam blushed, gently kicking Dean's foot under the table. "Shuddup, De." 

***  
Sometime later, as Dean was lounging on the couch with Sam's legs draped over his lap, John stood in front of the TV with his hands behind his back. 

Dean grunted a complaint, but sat up straight, curious about what John was holding. Seconds later, Dean was holding the keys to the Impala in his hands. 

"Felt like it was time for you to have her. S' why I got the truck. I know you'll take good care of her, son," John said before walking into his bedroom and closed the door. Sam, meanwhile, stood up and glanced at Dean. "Meet me in our room in like, 10 minutes, please. I wanna give you your gift..." 

***  
Exactly 10 minutes later, Dean had everything turned off in the house and was currently opening the bedroom door. The lights were dim, and Dean could just barely see Sam's lithe silhouette on the edge of the bed. 

"Y-You can turn on the light... Just lock the door first, please." 

Dean, slightly confused, obeyed, turning on the lights and gasping at the sight before him. 

Before him sat his little brother in red lingerie, cheeks a faint pink and slim, oh-so-feminine hips rocking down on something unseen to Dean from this angle. 

"Sammy, what- what is this? What're you sittin' on, babe?" Dean whispered in a breathless voice.

Some shifting later, and Sam bit his swollen pink lips as he turned around on all fours, showing Dean the thick, silicone dildo buried to the hilt in Sam's tiny body. 

"Holy... Sammy..." Dean whispered, cock straining and leaking against his jeans. 

"M-My birthday gift to you... I want you to make love to me, De... Please..."


	9. Chapter 9

**Summary for the Chapter:**

> Smut. Pure, underage smut.

Dean was hesitant as he walked over to his baby brother. Hesitant to touch him, hesitant to kiss him, hesitant to speak to him. 

It wasn't like they hadn't done things before, but lately they hadn't been so close. Samny had school, Dean had a normal job, and with John always home, the only free time they had was late at night. Usually that free time included lazy handjobs and sloppy kisses, both boys exhausted from long days. 

Tonight though, both of them were wide awake, alone, and horny. 

Dean sat on the edge of the bed beside Sam, who had fingers curled into the sheets as he rocked down on the toy inside of him. 

Dean reached out, sliding his fingers along Sam's quivering thighs, ghosting them over the flimsy fabric covering his cock. He slid his hands along Sam's sides, skimming them over his arms until he was cupping Sam's face with one hand, the other one pulling down the straps of his lingerie top. 

Once the top was pooled around Sam's hips, Dean bit his lip and tapped Sam's legs, silently telling him to turn. Sam obeyed, pushing aside the panties so Dean had access to the dildo. 

"Sammy... fuck you're such a cockslut, baby," Dean whispered huskily, pulling the dildo out and listening to Sam's delicious whimpers. He bit his lip, slamming the toy back in and bathing in the sound of Sam's muffled moans. 

Dean pulled the toy out completely, dropping it onto the floor and putting his palms flat on the twin globes of Sam's ass. Admiring the way Sam's now empty hole fluttered around air, he hooked his thumbs into the flesh and leaned in, blowing air over it and listening to Sam's breathless whines. 

Dean grinned and licked a stripe over Sam's hole, cock so hard it hurt by this point. "De- Dean st-stop teasing!" Sam hissed, and Dean watched the way his baby brother's body quivered as he pulled Sam's hole wider. Dean licked at the exposed flesh inside, cooing at Sam's sobs of need. 

"Where's the lube, Sammy?" he whispered, pulling one thumb out to swat at Sam's hole lightly. Sam cursed and squirmed, yanking open a drawer of the bedside table and throwing the small bottle of lube at Dean. 

Dean caught it in one hand before he pulled completely away from Sam, ignoring his protests. He drizzled some lube over his fingers, rubbing them together to warm it up before he eased two fingers into his brother effortlessly. 

"Oh god, Dean," Sam moaned out, toes curling as Dean scissored the digits slowly. 

"Fuck, Sammy you're so pretty..." Dean rasped, curling and twisting his fingers until they brushed over that sweet spot in his brother. 

Sam let out moans worthy of a porn star, rocking back on his big brother's fingers as his cock smeared precome all over the satiny panties he was wearing. 

Without stopping his motions on Sam's prostate, Dean added a third finger, listening to Sam begin to beg for his cock not soon after. 

Dean pulled his fingers out after a while and stood up, licking his lips as he stripped. "Can you take off those panties, babe?" he asked as he undid his jeans. 

Sam nodded and, without turning, pulled the panties down slowly and kicked them off. 

Dean let out a shaky breath as his cock, finally freed, slapped against his stomach. He climbed back on the bed and turned Sam onto his back, pushing his legs up to his ears. "Hold 'em there. Yeah, good boy..." Dean drawled as Sam hooked his arms around his thighs. 

Dean grabbed the lube and a condom, looking at Sam questioningly. "Condom or no? I'm clean, I know that for a fact." 

Sam shook his head, sweaty hair sticking to his forehead, lips shiny with spit, and face flushed the same shade of pink as his pretty little cock. 

Dean squirted lube onto his hand, spreading it over his cock generously before he lined up with Sam's hole. He pushed in, meeting little resistance, and was soon buried to the hilt. 

The heat of his Sammy was intense, and Dean had to pause for a moment, hands gripping Sam's hips as he took a deep breath. 

"Don't go slow, De. I like it rough." 

So Dean went rough. Headboard denting the wall rough, and Sam loved it. Moaning and whimpering and screaming Dean's name, Dean wondered why John wasn't banging on the door. 

It didn't take long for little Sammy to come all over himself, and the clenching around Dean's cock had him spilling his load right against Sam's oversensitive prostate. 

Dean pulled out when he was done, collapsing next to Sam and tugging the covers over them. "Happy birthday, De," Sam said groggily, looking utterly fucked out as he smiled at Dean. 

Dean smiled, rubbing circles into Sam's back as he drifted off. 

"I love you, Sammy. Now and forever."


	10. Chapter 10

**Summary for the Chapter:**

> John's gone longer than he prepared the boys for.  
> Dean has no choice but to convince the motel owner to let them stay longer.  
> Sam gets upset when he finds out.

"Don't worry boys, I'll be back in a week. Money's on the counter. Salt the door when you leave," John had said. His parting words were almost always the same when he left his sons alone. Sam and Dean had their automatic responses at the ready at this point, so no matter what they were doing, John always heard a chorus of "Bye Dad!" right before he closed the door on his two sons, none of them ever truly knowing if he'd come home alive.

***  
John had /promised/ he'd only be gone a week. Had even given the boys extra money just in case. But being gone for over a month? Sam and Dean sure as hell weren't prepared for that. Two weeks after John left, the motel owner was banging on their door, telling them their time was up, they had to go. Dean refused to let Sam hang around on the streets though, and after waiting for the owner to leave, he told Sammy he'd be back, he just had to take care of something. Sam's hazel eyes were full of distrust, but he nodded, because Dean was his big brother, and he knew he'd be okay. So Dean smiled and headed out, going straight to the front desk.

"Can I help you?" the extremely bored guy behind the counter asked, eyes dull and far off. Dean nodded, rubbing his arms lightly as he smiled at the guy. "I really need to speak to the owner about my room... Is he around?" Dean said softly. The guy waved Dean behind the counter and into a dingy office without batting an eye. The minute that door closed and the large guy behind the desk looked at him, Dean put on his innocently seductive expression, seating himself across from the guy- Garrett Turner, his nameplate read- and spreading his long teenaged legs just the right amount to draw Garrett's eye. "Look, Mr. Turner, my baby brother n' I, we need the room we're stayin' in /real/ bad... Our dad ain't back from his business trip, but we don't got any more money," Dean said, shifting slightly under the man's intense blue gaze.

Garrett nodded and studied Dean silently for a moment. "Well I don't have any open positions for you to fill until your dad gets back, unless you wanna be a maid," he said, chuckling slightly.

Sick bastard, Dean thought, he'd probably love to see Dean in a maid outfit. Hell, Dean would love to see himself in a maid outfit honestly. But the sight was not for this scumbag's eyes. 

"W-well is there anything else I could do? I'm desperate, sir. I'll do /anything/ to stay here," Dean said, leaving the innuendo hanging in the air between them. 

Garrett gave Dean a quick once over before standing up and walking over to the young man. Dean watched Garrett's fingers expressionlessly as they felt Dean's body—his arms, torso, legs, and finally his crotch, which was unintentionally hard from the vaguely sensual touches. "Mm, you seem pretty experienced in giving people what they want so you can get what you need. So uh, you wanna stay here so bad? You're gonna be in here for while," Garrett purred in Dean's ear. Dean just nodded, going on autopilot to hold in his emotions as he let Garrett manhandle him however he wanted. 

***

Garrett definitely wasn't exaggerating when he said Dean would be in there for a while. Who knew two more weeks of staying in a shithole motel cost a /lot/ of painful, kinky, disgusting sex. Dean had went into the office at about 3 pm, and left at 8 pm, probably looking throughly fucked out, with his limp, glazed over eyes, and God knows how many hickeys, scratches, bruises, and rugburns. 

He just smiled at the surprised, and slightly disgusted, bellhop before limping off to his room. Dean stopped outside the door and leaned on it, closing his eyes briefly as he thought of what the hell to say to Sam. 

He didn't have very long to think though, because minutes after Dean reached the door, it was flung open, sending Dean to his knees in front of his brother. 

"I'd ask you were the hell you've been for five hours, but the way you smell tells me everything. God, Dean why can't you get a normal job?" Sam said, helping his big brother to his feet. 

Dean leaned on Sam and took his hand gently. "This was quicker. If I got a normal job, we'd still be on the streets. Now can you just... help me shower?" Dean asked.

Minutes later, Dean was seated in a bathtub full of warm water, Sam scrubbing at his hair with the motel's sweet-smelling shampoo. 

Neither brother said anything for a long time, Sam too upset, and Dean battling with his own self-hatred and depression to try and explain his sick way of keeping Sam in a somewhat safe impermanent home.

After a long ten minutes, Dean finally looked at Sam, at his determined expression, at his hazel eyes always full of love and compassion, at his soft features yet to experience puberty, and Dean knew that no matter what happened to him, Sammy had to always be safe. Always.


	11. Chapter 11

**Summary for the Chapter:**

> Flash-forward in time.  
> Dean's 20, Sam's 16.  
> Just some deeper insight into Dean's mind.

Dean didn't really know what had first made him decide to start selling himself, of all things. He could've done anything. Gotten a job, asked friends for money, anything. And yet, he chose to prostitute himself.

It's not like Dean enjoyed it. Sure, he liked the feeling of a dick up his ass, but the way he was treated? It was disgusting. But, Dean supposed in some sick and twisted part of his mind, he did like it. He felt like he deserved being treated like some trashy slut on the street. Which is exactly what he was.

Who the hell decides 'You know what'd be a great way to get money for my little brother? Prostituting myself!' A sicko. That's who. 

Dean was just a disgusting burden. His dad, Sam, everyone would be so much better off without him, right? 

No. Dean knew Sam, knew how ruined he'd be if anything happened to Dean. The kid already spends half his time cleaning Dean up when he drags himself home from a random fuck. The othet half is spent at school. If Dean offed himself, it wouldn't help anything. The only way any of this could be fixed is to stop going out. Get a job. Ration the money more. It'd make John less stressed out about what his son's doing while he's on a hunt, Sam would be able to focus on school, and Dean wouldn't come home covered in God knows what, unable to bathe himself without Sam's help.

***

After months of fighting these thoughts, these lingering whispers of "Just kill yourself. Get it over with. All you are is a disgusting, tainted man. Nobody would even care that you were gone.", Dean broke. He walked into the bathroom, smashed his razor, closed the door, and shakily pressed a blade to his skin.

He stared at his pale, guant face in the mirror and really /looked/ at himself. He'd really changed. His hair was lank and greasy, his eyes dull and bloodshot, ringed with dark circles, and his neck ringed with bruises and hickeys. Is this really what he'd become?

Dean nodded to himself, sighing shakily as he slowly applied pressure to the blade, feeling it slice through the first few layers of skin. Now, all he had to do was drag it down. 

Just as he started to drag the blade down, Dean heard the motel room's door open, and Sam's voice calling his name. 

Dean felt tears prick at his eyes as he stared at the blood trickling from the cut on his arm. He shook his head, pulling the blade back and rinsing off the cut, relishing in the stinging pain.

Maybe he could just do it in smaller steps. He set the razor blade down and opened the bathroom door a crack. "S-Sammy? Hey, just give me a few and I'll out," Dean said, keeping his voice steady. After hearing Sam's okay, he picked up the blade again, and rolled up his jeans. 

Dean leaned on the wall, staring at the unmarked skin of his leg before shrugging, pressing the blade into the flesh of his calf, dragging it across agonizingly slow, panting softly as he lost himself in the pain. 

He dragged it across the skin seven times, one time for every year he'd been selling himself.

After cleaning his leg off and wrapping it in gauze, he hid the blades in a drawer and walked out of the room. 

"Heya Sammy, how was school?" he asked, pasting a smile on his face as he pulled Sam into his arms. 

As he listened to Sam talk in his arms, he set a date. Two months from now he'd do it. 

Two months, and he'd finally have bliss, and his family would be happy again.


	12. Chapter 12

**Summary for the Chapter:**

> Dean's set date grows near. 
> 
> Last chapter before the epilogue.

Dean had been counting the days down to the date he'd set. He had everything planned out, except for how to actually /do/ it. Should he overdose? Cut his wrists? Cut his neck? Hang himself? Shoot himself? 

None of the choices were very pleasant, but neither was dying. He just kept the decision at the back of his mind, making sure to stay as happy as he could around his Sammy.

Thankfully, Sam didn't notice anything off, and John was sinking further and further into his alcoholism, which meant he didn't really focus on his boys anymore. 

Dean wasn't too upset though, it made it easier to get away with the cutting. Dean knew it was wrong, knew he should stop, but he'd be dead in two weeks anyway, so what was the point. 

By now, Dean had stopped going out, which set Sam at ease, and he didn't own any more skirts, panties, or assorted lingerie. 

It felt like a weight off his chest, actually, and there were occasions where he could actually find himself genuinely happy with his life. It wasn't long before the depression shut those thoughts down, though, leaving Dean back in the dark where he always was. 

Sam was a lot more affectionate, willingly kissing Dean, although the elder Winchester refused to let Sam see below his thighs anymore, so their alone time was spent with Dean's jeans above his knees and Sam's hot mouth on his cock.

Some nights, after a particularly hot blowjob, handjob, or rimjob, Dean couldn't help but think about Sam's future. As he held his brother/best friend/lover, he wondered if Sam would ever be in a normal relationship. If he'd ever find a girl or boy to be normal and happy with. 

Those thoughts made Dean feel happy, warm, but also made him feel even more alone. Even with Sam's warmth right beside him, Sam's arms around him, he was always alone. Most nights were him crying himself to sleep, Sam fast asleep beside him and John snoring in the other bed. 

He'd have to say his goodbyes soon. 

***

One more week. One more week on Earth. Dean wondered if he'd end up in Heaven or Hell. Probably Hell, since he was fucking his little brother. 

Now, Dean spent every waking moment with Sam, making the most of their short time together. 

He didn't stop the cutting. His legs were covered from the knee down in fresh cuts, old cuts, and pink scars. Dean loved the way they looked. Loved feeling his pants catch on them. Loved the pain. Maybe he was sick. He couldn't find it in himself to care.

Dean decided he'd shoot himself. While Sam was at school and John was at work, he'd put a bullet in his brain on November 2nd. 

It took Dean a while to realize the irony of the date. But now when he thought of dying on the day his mom died, he felt comforted. Maybe they'd meet in the afterlife. 

Probably not. Dean's such a fuck-up, Mary'd do anything to avoid her son, right? 

***

Today was the day. Dean was up early, made sure John left, kept Sam home for another hour, fucked him. Sam saw the cuts. Sam tried to talk about the cuts before he left. Dean just told Sam he loved him and closed the door in his face. 

He waited another 30 minutes to make sure Sam wouldn't come back. He started packing his clothes in his duffel, pretending he was just packing for a normal trip. Tears were blinding him, but he was so detached from himself, he didn't bother to wipe them away.

Setting his packed duffel on his and Sam's shared bed, he grabbed a sheet of paper. Stared at the words he'd written. Nodded, satisfied that it explained everything. 

He grabbed his gun, tears falling harder now, and looked around. He sat down on his bed, cross-legged and in his favorite outfit, he clicked the safety off, put his finger on the trigger, and put the gun in is mouth. 

He closed his eyes, because who wants to come home to find your dead son, your dead brother, staring lifelessly. No. Eyes closed. More peaceful that way. 

One last thought. One last thought before he couldn't think anymore.

'Keep them safe.'

Then, Dean Winchester pulled the trigger.


	13. Epilogue

**Summary for the Chapter:**

> Just tying up loose ends.

_"DEAN! Oh g-god D-Dean what have you done?!"_

_"Sammy you need to let go. We have to... we have to burn the body."_

_"N-No! He's n-not dead, he can't be dead, Dad! We n-need him... I need him..."_

_"Sam—dammit Sam get off him! We need to go before the police arrive. C'mon, get up now."_

_Sam was limp as his father pulled him off his brother's body. His Dean, his Dean was dead._

_"Wh-why didn't he say anything to me?! All this time I thought he was getting better, not worse! N-now he's **dead**."_

_John looked at his boy, his 16 year old son, already having seen so much, and now to come home to see his brother dead. John wished it could have been different. But hey, at least Dean would see his mother in heaven._

**———————————**

Two years. Two years without his brother by his side. Sam wasn't sure how he himself was still breathing. He'd refused to let John burn Dean's necklace, or his ring, saying he needed something besides a picture to remind himself of his once happy, breathing, loving brother. 

Tonight, he held the necklace in his hand, and stared at the fire in front of him. The horns of the amulet cut into his palm, but he couldn't bring himself to care. 

John was seated across from him, watching him over the fire. "You'll regret it. I know you will, Sam. I've been down this road before."

Sam looked at his father, registered his words. He stood, stepped closer to the fire, and held the amulet above the flames. 

"All it does is remind me that he's dead. That he's not coming back. It doesn't remind me of happiness anymore," Sam said quietly. closing his eyes as he let his fingers open. 

John was quick though, grabbing the necklace before the flames devoured it. "Dammit Samuel! Keep the goddamn necklace! Keep the necklace, keep the ring, keep the goddamn pictures and don't you _ever_ let them go. Don't forget what he looked like, how he smiled, how he talked, just... hold on to those memories until you can see him again," John said, voice growing softer toward the end. 

Sam would've seen the tears falling from his father's eyes if he looked up. He didn't, though. He just stared at the ring on his finger, at the necklace gripped in his hand, and nodded before putting it back on. 

He kept his head down as he walked back to the Impala, stared out the window as John drove them to the next motel. He stared at the sky, hoping Dean was up there, hoping they'd see each other again one day. 

One long nap full of Dean later, he was sitting on a motel bed, digging through his duffel. 

He hesitated when he touched what he was looking for, closed his fingers around the edge. Then, he pulled out the papers. Read them like he'd read them a thousand times before. Then he stood. Walked over to John. Waited to be noticed.

When John looked up, he set the papers over John's journal and spoke before John could. 

"I got accepted into Stanford. And I'm going." 

Sam knew Dean would have wanted this for him, which made him stronger, bolder. Ready to face his dad. 

'Are you listening Dean? Are you proud?'

**Notes for the Chapter:**

> So uh, yeah. That's the end of TTWDFL. I hope you enjoyed. I'll try to start up another fic soon, but we'll see how well my creative juices are flowing. 
> 
> I enjoyed writing this, and I know there could've been more, but there's only so much dirty sex a guy can write, y'know?
> 
> So yeah, the end, I guess. Keep an eye out for another fic at some point guys. Bye!


End file.
